If the claim of reissued letters patent No. 4321, Division B,
granted to Charles Graebe and Charles Liebermann April 4, 1871, for
an "improvement in dyes or coloring matter from anthracine" (the
original patent, No. 95,465, having been granted to them October 5,
1869), namely:
"Artificial alizarine, produced from anthracine or its
derivatives by either of the methods herein described, or by any
other method which will produce a like result,"
is construed so broadly as to cover a dyestuff, imported from
Europe, made by a process not shown to be the same as that
described in No. 4321 and containing large proportions of coloring
matters not shown to be found to any practically useful extent in
the alizarine of the process of No. 4321, such as isopurpurine or
anthrapurpurine, it is wider in its scope than the original actual
invention of the patentees, and wider than anything indicated in
the specification of the original patent. If the claim is to be
construed so as to cover only the product which the process
described in it will produce, it does not cover a different product
which cannot be practically produced by that process.
This was a suit in equity for the alleged infringement of a
patent for improvement in dyes from anthracine. The nature of the
invention, the extent of the claims, and the facts which went to
show the infringement or to affect the validity of the patent are
fully brought out in the opinion of the Court from the large mass
of testimony in the record. Judgment below sustaining the validity
of the patent, from which the alleged infringers appealed.
Page 111 U. S. 294
MR. JUSTICE BLATCHFORD delivered the opinion of the Court.
This is a suit in equity, brought in the Circuit Court of the
United States for the Southern District of New York, by Badische
Anilin and Soda Fabrik, a corporation organized under the laws of
the Grand Duchy of Baden, in the Empire of Germany, against the
appellants, for the infringement of reissued letters patent No.
4,321, granted to Charles Graebe, of Frankfort on the Main, and
Charles Liebermann, of Berlin, Prussia, April 4, 1871, for an
"improvement in dyes or coloring matter from anthracine." The
original patent, No. 95,465, was granted to the same persons
October 5, 1869, for an "improved process of preparing alizarine."
It was reissued on two separate amended specifications, Division A
and Division B. No. 4,321 is Division B.
The following is the text of the specifications of No. 4,321 and
No. 95,465. Reading in it what is outside of brackets, and what is
inside of brackets, omitting what is in italics, gives the
specification of No. 4,321. Reading what is outside of brackets,
including what is in italics, omitting what is inside of brackets,
gives the specification of the original patent:
"Be it known that we, Charles Graebe, of Frankfort on the Main,
and Charles Liebermann, of Berlin, in the Kingdom of Prussia, have
invented a [new and useful improvement in the manufacture of
alizarine;] process for preparing alizarine from anthracine, and we
do hereby declare the following to be a full, clear, and exact
description thereof, which will enable those skilled in the art to
make and use the same. We first change the anthracine into
anthrakinon (oxanthracine), a substance known to [the] chemists by
the investigations of Anderson. For this purpose we take one part,
by weight, of anthracine, two and a half parts, by weight, of
bichromate of [potash,] potassa, and ten or fifteen parts, by
weight, of concentrated acetic acid, and we heat these substances
together in a vessel, either of glass or day, to about 100�
centigrade to 120� centigrade, till nearly all of the
bichromate
Page 111 U. S. 295
of [potash] potassa is dissolved and the liquid has acquired a
deep green color. We then recover the acetic acid not consumed in
the reaction by distillation, and treat the residuum with water to
remove the chromic acetate. From the insoluble mass we obtain the
anthrakinon in a pure state by distilling the whole from a retort
of glass or iron. In the place of the acetic acid, sulphuric acid,
diluted with one or two parts of water, may be employed. Instead of
the method just described, we also employ the following one: we
heat the anthracine in a vessel of glass or of clay, with ten parts
of concentrated acetic acid, to about 100� centigrade, or a little
higher, and we add nitric acid of about 1.3 specific gravity in
small portions till the violent reaction ceases. After distillation
of the acetic acid, we purify the residuum, as before. We then
convert the anthrakinon, prepared by one of the methods described,
into bibromanthrakinon. For this purpose, we take three parts of
anthrakinon, five parts of bromine, and we heat these substances
for ten or twelve hours, or until nearly the whole of the bromine
has disappeared, to a temperature, by preference, of about 100�
centigrade, in a suitable close vessel, either of glass or enameled
or glazed iron, which is capable of sustaining the pressure [which
is] generated by the reaction. The apparatus is then allowed to
cool. It is opened in order to permit the escape of [bromic]
hydrobromic acid, which can be recovered by absorption either in
water or in an alkaline solution. We purify the bibromanthrakinon
remaining in the vessel, as a solid substance, by crystallization
from benzole. Instead of the method above described for preparing
bibromanthrakinon, we also employ the following: we convert first
the anthracine into a bromine derivative, into the
tetrabromanthracine, known to chemists by the investigations of
Anderson. We take one part of this tetrabromanthracine, and we heat
it in a retort of glass or day with about five parts of nitric acid
of about 1.3 specific gravity to 100� centigrade, as long as vapors
of bromine are evolved. We distill off the greater portion of the
nitric acid, wash the residuum with water, and purify it by
crystallization from benzole. We thus receive the bibromanthrakinon
as before, in the form of a yellow, solid mass. We then convert the
bibromanthrakinon into alizarine. For this purpose, we take one
part of bibromanthrakinon, two to three parts of caustic potash or
soda, and so much water as is necessary to dissolve the alkali,
and
Page 111 U. S. 296
we heat the whole in an open vessel of glass, glazed or enameled
iron, or silver, to about 180� to 260� centigrade for one hour, or
[till]
until the mass has acquired a deep blue color. We
then dissolve it in water and filter the violet solution, from
which we precipitate the alizarine by
an inorganic or
organic acid. We collect the yellow flocks of alizarine
thus obtained on a filter and wash them with water. By these
methods we receive the alizarine in a form in which it can be
employed in the same manner as the different preparations from
madder. In the place of bromine, chlorine [also] may
also
be employed, but not so conveniently, as the reactions above
described are more difficult to accomplish with chlorine than with
bromine.
Having thus described the nature of our invention and
the manner of performing and carrying out the same, we would have
it understood that we do not confine ourselves to the exact details
hereinbefore given."
The claim of No. 4,321 is as follows:
"Artificial alizarine, produced from anthracine or its
derivatives by either of the methods herein described or by any
other method which will produce a like result."
The claim of the original patent was in these words:
"The within-described process for the production of alizarine,
by first preparing bibromanthrakinon or bichloranthrakinon, and
then converting these substances into alizarine, substantially as
above set forth."
The bill of complaint alleges that No. 4,321 was issued "for a
distinct and separate part of the same invention, on a corrected
specification," on the surrender of No. 95,465, and No. 4,321
states on its face that on such surrender, new letters were ordered
to issue "on two separate amended specifications." But Division A,
No. 4,320, is not in the record before us. The bill alleges the
infringement to have been committed by making, selling, or using
the invention or dyes containing it. The answer denies the
manufacture of alizarine, but avers that the defendants have sold
in the United States alizarine lawfully made in Germany and
imported as an article of commerce, which was not made by the
process described in No. 4,321 or any process substantially the
same, but was made according to processes which were invented
subsequently to the date of No. 95,465, and are the subject of
different and independent letters
Page 111 U. S. 297
patent. The answer also avers
"that alizarine is a natural product, having a well known
definite constitution; that it is not a composition of matter
within the meaning of the statute, but has been well known in the
arts from time immemorial for the purpose of dyeing, and has
generally been extracted from 'madder root' and from other
analogous products by various processes suitable for that purpose;
that therefore there can be no valid patent granted for alizarine,
and that No. 4,321 is void."
The answer refers to "Watts' Chemical Dictionary, published
before 1869, under the title "Alizarine," to show that alizarine
was well known long before the said patent," and also sets up that
the patent had expired because prior patents granted to the
patentees in foreign countries for the same invention had
expired.
Proofs were taken and, on final hearing, the circuit court
decreed that No. 4,321 was valid and had been infringed, and
ordered a reference as to profits and damages and a perpetual
injunction against the making, using, or selling of the article
designated in No. 4,321 "artificial alizarine," or dyes containing
the invention described in and secured by No. 4,321. Afterwards
there was a final decree against the defendants for $13,326.65 and
costs, of which $12,871.86 was for profits made by the defendants
"by the sale of artificial alizarine in infringement" of No. 4,321.
From this decree the defendants have appealed.
This reissued patent No. 4,321 had been adjudicated in the
circuit courts in several cases. It was before the Circuit Court in
Massachusetts in February, 1878, and the decision of Judge Shepley
is in
Badische Anilin and Soda Fabrik v. Hamilton Mfg.
Co., 3 Bann. and Arden 235, and 13 Off.Gaz. 273. It was also
before the Circuit Court for the Southern District of New York in
September, 1878, and the decision of Judge Wheeler is in
Badische Anilin & Soda Fabrik v. Higgin, 15 Blatchford
290, and 3 Banning & Arden 462, and 14 Off.Gaz. 414. The
decision of Judge Wheeler in the present case in April, 1879, is in
16 Blatchford 155, and in 4 Banning & Arden 215. The patent was
also before the Circuit Court in Massachusetts in September, 1879,
and the decision of Judge
Page 111 U. S. 298
LOWELL is in
Badische Anilin & Soda Fabrik v.
Cummins, 4 Banning & Arden 489. In all of these cases, the
validity of No. 4,321 was sustained.
In the case before Judge Shepley, it was held that No. 4,321 was
a valid patent for a manufacture and composition of matter, an
artificial dyestuff called artificial alizarine, being a new
product, produced by a new process, not a chemically pure
alizarine, but having combined with the alizarine in it,
anthrapurpurine, isopurpurine and other bodies, not known to have
existed before they were produced by Graebe and Liebermann, the
presence of some of which bodies appeared to much enhance the value
of the dyestuff. It was decided that the defendants had used that
article.
In the case against Higgin, it was held that the product of the
process described in No. 4,321 contains isopurpurine,
anthrapurpurine, monoxanthraquinone and other ingredients, which
were not only not ingredients in pure alizarine or madder
alizarine, but did not exist in any dyestuff with chemically pure
alizarine, C14H8O4, before that of Graebe and Liebermann, and are
useful coloring agents, so that the product invented is a new
composition of matter. It was decided that the defendants had used
or sold dyestuffs substantially the same, though claimed to be the
product of a different process.
In the present case, it was insisted in the circuit court by the
defendants that the patented product was the same thing as the
natural dyestuff, alizarine, found in the root of the madder plant,
and chemically known by the formula C14H8O4, and not patentable.
But it was decided that the article which Graebe and Liebermann had
made synthetically from anthracine, though having the same chemical
formula as madder alizarine, was essentially different, in
capabilities and properties, from chemically pure alizarine, madder
alizarine, or any coloring matter before known; that the article
dealt in by the defendants was produced by the process of United
States letters patent No. 154,536, granted July 28, 1874, to
Heinrich Caro, Charles Graebe, and Charles Liebermann; that the use
of sulphuric acid in the process of the latter patent performs the
same office in the same way as the
Page 111 U. S. 299
bromine in the process of No. 4,321, and that the products of
the two processes are identical.
In the case before Judge Lowell, he held that what Graebe and
Liebermann sought to discover and supposed they had discovered was
the alizarine, which is the dyestuff of madder; that what is called
"artificial alizarine" contains important dyeing substances not
found in madder -- namely anthrapurpurine and isopurpurine
(accordingly as these may be two substances or one and the same
substance) and flavopurpurine, which substances produce valuable
effects not produced by any extracts from madder; that although the
defendant insisted that those new purpurines were not found in the
artificial alizarine made by the bromine process of No. 4,321, and
were found only in artificial alizarine made by methods invented
since Graebe and Liebermann invented that process, and the evidence
on that point was in much conflict, yet it was shown that pure
alizarine, pure isopurpurine, and pure flavopurpurine were all
contained in the patented article; that the artificial alizarine of
No. 4,321 is different in some important respects from any article
known before; that the new article of manufacture claimed in No.
4,321 was new in fact, and that the infringement was made out.
In Watt's Dictionary of Chemistry, vol. 1, p. 113, published in
1866, Alizarin is stated to be a red coloring matter obtained from
madder, first prepared by Robiquet and Colin. This was in 1826. The
correct formula of alizarine, C14H8O4, was first arrived at by
Strecker in 1866. It means that there are 14 atoms of carbon, 8
atoms of hydrogen, and 4 atoms of oxygen in each molecule. At this
stage, Graebe and Liebermann took up the subject and treated madder
alizarine with the view of determining what was its mother
substance. They tell the story themselves, in a paper in the
record, entitled "Artificial Alizarine," which is a translation
from the original, prepared in German by them, contained in the
Official Report of the Vienna Exhibition of 1873 and also published
separately in 1876. They heated madder alizarine with zinc dust,
and made the alizarine give up its four atoms of oxygen, and take
up two atoms more of hydrogen. They thus obtained a hydrocarbon,
identical with that found in coal tar, called anthracine
Page 111 U. S. 300
and having the formula C14H10. They then conceived the idea of
converting anthracine into alizarine. Anthracine was difficult to
obtain, and the experiment was conducted on a small scale. But it
resulted in the process, described in No. 4,321, of converting
anthracine into anthrachinon, the formula of which was C14H8O2, and
then heating the anthrachinon with bromine and obtaining
bibromanthrachinon, and heating that with caustic potash or soda,
and obtaining alizarine. Graebe and Liebermann thus solved the
problem of the synthesis of alizarine. It was a matter of great
scientific interest, and gave thus solved the problem of the that
the first method, described in No. 4,321, for preparing the
bibromanthrakinon was so laborious that they devised the other
method described, of first converting anthracine into
tetrabromanthracine, and then treating that with nitric acid to
obtain bibromanthrakinon. "This method," they state, "made it
possible to obtain the alizarine more readily, and aroused hopes of
its technical execution," although it involved two more reactions
than the first method.
In regard to the alizarine thus obtained, the same paper
says:
"The artificial alizarine, besides having the same composition,
had also the same properties as vegetable alizarine. In hydrated
alkalies it is soluble, with a blue violet to purple color. The
solutions of the alkali salts give, with lime, baryta, lead, iron,
alumina, and tin salts, lakes corresponding to the madder lakes.
Cloth printed with mordants dyes exactly alike with both coloring
matters. From these salt-like compounds yellow floculent alizarine
is set free by the addition of a mineral acid. The artificial
coloring matter shows the same solubilities, and the solutions of
the alkaline salts the same absorption spectra, which are known of
the natural coloring matter. The free coloring matter sublimes in
beautiful yellow to red needles, which cluster together like
feathers. On oxidizing with nitric acid, phthalic acid and oxalic
acid are formed. Heated with zinc dust, the artificial alizarine is
again converted into anthracine."
The paper then proceeds:
"The above methods, which now, from a technical point of view,
have only a historic interest,
Page 111 U. S. 301
and are therefore described without further detail, make up the
subject of the patents taken out in England on the eighteenth of
December, 1868, and then also in France, Prussia, most German
states, Austria, Russia and America."
The provisional specification deposited in the English Patent
Office, December 18, 1868, which was the date of the patent, gives
a short description of the process, and says:
"The alizarine prepared in this artificial way is perfectly
pure, and can be employed in all the applications for which the
different preparations of madder are used."
The full specification, filed June 17, 1869, is substantially
identical with the specification of No. 95,465, and claims
"the artificial production of alizarine, by first preparing
bibromanthrakinon or bichloranthrakinon, and then converting these
substances into alizarine, as herein described."
In further pursuing the history of the matter the same paper
proceeds:
"The discoverers of the synthesis of alizarine soon found it
necessary to enter into connection with some large dye factory.
This was necessary in order that the raw material could be more
easily obtained and that the experiments could be made on a large
scale and further developed. This could be done best with an
establishment already in existence, where the doubtful question,
whether this might be the basis of an industry, with hopes of
success, could be solved. One of the chief difficulties experienced
was the fact that the raw material was not only known in commerce,
but also in the tar industry, and it was difficult to say whether
it could ever be obtained in sufficient quantity. It was also
doubtful whether the artificial alizarine could compete with the
natural. Furthermore, there was much difficulty in transferring the
above methods to a large scale. Graebe and Liebermann therefore
entered into connection with the Baden Anilin and Soda Works, in
Ludwigshafen, on the Rhine, the largest works of the kind in
Germany, even on the Continent. [Originally, the experiments were
limited to the purification of the anthracine and the manufacture
of anthrachinon by the second mentioned bromine method, because
this, notwithstanding its difficulties, showed some hopes of
success.]"
The passage above in brackets, by
Page 111 U. S. 302
another translation, reads thus:
"The first trials principally embraced the purification of
anthracine, the manufacture of anthrachinon, and the practical
application of the second above-mentioned bromine method, as the
same, notwithstanding the great difficulties, still gave assurance
that it could be used practically."
The paper then goes on: "The latter" (meaning the second
mentioned bromine method)
"was dropped as soon as the observation was made that the
alizarine could be made more simply by means of anthrachnion
sulpho-acids. Graebe and Liebermann had originally attempted to
obtain anthrachinon sulpho-acids by acting on anthrachinon with
sulphuric acid. But they made the mistake of using too low heats.
The temperatures they employed were not high enough, being not
greater than those generally employed in the preparation of
sulpho-acids. They had also been misled by the observation that
anthrachinon could be sublimed unchanged from strongly heated
sulphuric acid. Therefore they hoped little from sulpho-acids, and
gave all their attention to improving the above methods. This
mistake was avoided, and the modification of the synthesis of
alizarine, which forms the basis of the industry of today, was
discovered first by Heinrich Caro, who, as an officer at the Baden
Anilin and Soda Works, made it his task to give, in combination
with Graebe and Liebermann, life to the alizarine industry. Caro
first noticed that anthrachinon, if heated with sulphuric acid to
above 200, would give sulpho-acids, which, on fusing with hydrate
of potash, formed alizarine, the same as the bromine compound.
Perkin noticed the same fact shortly after or at about the same
time. This method was further developed by Caro and the original
discoverers, and the English patent was taken on June 25, 1869
(Caro, Graebe and Liebermann, English patent, 1869, No. 1,936). The
patent of Perkin is dated June 26 (Perkin, English patent, 1869,
No. 1,948). Two methods were discovered, analogous to the two
bromine methods. In the first and most important, the anthracine is
oxydized to anthrachinon; this is converted into sulpho-acids by
heating with sulphuric acid to 200� to 260�, and these, by the
beautiful method of Kekule, Wurtz,
Page 111 U. S. 303
and Dusart, by fusing with caustic potash or soda, are converted
into alizarine. The first process is therefore identical with the
first bromine method given above. In the second method, the
sulphuric acid acts on the anthrachinon in such a manner that,
besides the anthrachinon monosulpho-acid as principal product, a
small amount of anthrachinon bisulpho-acid is also formed. This was
subsequently determined analytically by Graebe and Liebermann. In
the patent, only the anthrachinon sulpho-acids are mentioned. From
analogy, Perkin, in his paper (Jour.Chem.Soc.(2) viii, 133, and
Ann.Chem.Pharm. clviii. 335), considered the bisulpho-acid only. It
is also formed in larger quantity by the excess of acid he employs
in his method than it is by the method of Caro, Graebe, and
Liebermann."
The reactions in the second method are then given by formulas,
in reference to anthrachinon monosulpho-acid and anthrachinon
bisulpho-acid, and it is then said:
"On fusing the two sulpho-acids, they give alizarine, exactly
like the monobrom- and bibrom-anthrachinon. The anthrachinon
bisulphoacid behaves for the greater part, if not altogether, like
the monosulpho-acid, and furnishes, instead of the corresponding
bioxyanthrachinon,"
(which is the alizarine of the process of No. 4,321),
"essentially trioxyanthrachinon, the isopurpurine." They then give
the two sets of chemical equations, one producing alizarine and the
other producing isopurpurine. Further on in the same paper they
say:
"As far as has been observed, it seems that only the
anthrachinon monsulpho-acid will produce alizarine, while the
anthrachinon bisulpho-acid produces isopurpurine."
In an article by Graebe in the New Handbook of Chemistry,
published in 1871, he had said:
"Alizarine, lizaric acid, madder red, matiere colorante rouge,
first prepared from madder by Robiquet and Colin (1826);
artificially by Graebe and Liebermann. (1868), from anthracine,
formula, C14H8O4, is derived from anthracine, and is to be
considered as byoxyanthrachinon, C14H6(O2)''(OH)8."
In another publication by Graebe and Liebermann in 1868, they
had said:
"By treating alizarine with zinc dust, a hydrocarbon
Page 111 U. S. 304
was produced having the composition C14H10 and coinciding
exactly in its properties with anthracine. . . . According to our
experiments, alizarine, which is hence a derivative of anthracine,
must have the formula C14H8O4."
In another publication by them, in 1869, they had said:
"We have produced from anthracine artificial alizarine. The
properties of the product obtained by us, as well as the colors
which we have produced with the same on mordanted cotton, exhibit
perfectly the identity of the artificial alizarine with that
obtained from madder root. . . . The methods which have led to the
above results, and which we shall describe later, confirm the
accuracy of the rational formula for alizarine recently advanced by
us."
Again, in a further publication in 1869, they had said:
"In our first notice, we have already hinted that we have
detected no difference between the natural and artificial
alizarine, and that the very characteristic colors which both
possess, when fixed on cotton mordanted with alumnia and iron, are
perfectly identical. We believe, therefore, that it is with one and
the same chemical individual we have to deal, and not with
isomerous compounds, of which an extraordinarily great number is
conceivable, and of which an example already exists, as we have
hinted, in chrysophanic acid. In conclusion, we will call attention
to the fact that our production of alizarine is the first example
of the artificial formation of a coloring matter occurring in
plants."
The various papers thus referred to are, it is understood, put
in evidence by stipulation with like effect as if the authors of
them had testified to the facts stated in them.
In Prussia, a patent for five years was granted to Graebe and
Liebermann, March 23, 1869, for their bromine process on condition
that it should be put into practical operation in twelve months
within the kingdom. On the 7th of July, 1870, after several notices
to them, the patent was declared extinct because proof had not been
produced of the carrying out of the patented methods. In view of
what Graebe and Liebermann themselves state in the publication
before cited, it is manifest that the Prussian patent was revoked
because the process described was not a practical one. There was
nothing
Page 111 U. S. 305
practical until the sulpho-acid discoveries were made. In regard
to this, the paper first cited says:
"The patent of Caro, Graebe and Liebermann is dated one day
earlier than that of Perkin. If any value at all is to be placed in
the date, then Caro must certainly be mentioned first, since the
application for a patent by the German chemist was delayed by an
error. The signing took place at the patent agent's in Berlin. In
reference to the above two English patents, Perkin and the Baden
Anilin and Soda Works, proprietors of Caro and Graebe and
Liebermann's patent, made an agreement in consequence of which the
patents became common property. By the publication of these
patents, the sulpho-acid methods of preparing alizarine became
known, and a series of works were erected in states which gave no,
or insufficient, protection to the patentees."
This shows that the only methods practiced commercially were the
sulpho-acid methods. The English patent for the bromine methods
expired December 18, 1871, for the want of payment of a further
fee.
The statement of Graebe and Liebermann is that Caro discovered
that by using anthrachinon with sulphuric acid, he could obtain
sulpho-acids, and then, with hydrate of potash, procure alizarine,
"the same as the bromine compound" -- that is, the alizarine of the
process of No. 4,321; but that the bisulpho-acid process, developed
by Perkin, produces not the alizarine of the process of No. 4,321,
which is bioxyanthrachinon, but trioxyanthrachinon or isopurpurine.
The article sold by the defendants is this last substance, made by
the bisulpho-acid process, carried on abroad at the present day and
containing large proportions of coloring matters not shown to be
found to any practically useful extent in the alizarine of the
process of No. 4,321, such as isopurpurine or anthrapurpurine, one
or both -- two articles if they are different, or one if they are
the same, as seems to be shown. No. 4,321 furnishes no test by
which to identify the product it covers except that such product is
to be the result of the process it describes. The process by which
the defendant's article is made is not shown to be the same process
as that described in No. 4,321. Graebe and Liebermann, as appears
from their own statement, experimented
Page 111 U. S. 306
with sulphuric acid and failed. It was not obvious that
sulphuric acid would accomplish any result, nor was it obvious how
to employ it. Their experiments with it led them to hope little
from it, and to withdraw their attention from it and devote
themselves to improving the bromine and chlorine methods. They
state that Caro avoided their mistakes, and was the first to
discover the modification which led to success, and that Perkin was
an independent discoverer of it about the same time. It is
therefore impossible to say that the sulphuric acid process was a
known equivalent process at the time. It is easy now, after the
event, for scientific men to say, with the knowledge of today, that
the thing was obvious. But the crucial facts contradict the
assumption.
It does not satisfactorily appear that the process of No. 4,321
will produce the defendant's article to any useful extent, if at
all. The process of No. 4,321 never was, and is not now,
practically carried on anywhere. The article of No. 4,321 was
called "artificial alizarine," and the article now in the market is
called by the same name, but the identity, in the sense of the
patent law, between them and between the processes for producing
them is not shown.
The English patent to Caro and Graebe and Liebermann having been
granted June 25, 1869, and the full specification filed January 13,
1870, an application for a patent in the United States for
producing artificial alizarine by the sulpho-acid processes was
filed by them January 26, 1870. It was granted as No. 154,536, July
28, 1874. The full specification of the English patent and that of
No. 154,536 are identical. The specifications state that the
invention relates to improvements on the invention described in the
English patent to Graebe and Liebermann of December 18, 1868, and
in No. 95,465, "in which the preparation of artificial alizarine is
based upon the action of caustic alkalies upon bibromanthrakinon or
bichloranthrakinon." They then proceed:
"We have now discovered that a similar result may be obtained by
substituting sulphuric acid for bromine or chlorine in the above
process. We thus obtain the sulpho-acids of anthrakinon, which, by
being dissolved in and heated with an excess of caustic alkali,
Page 111 U. S. 307
are converted into alizarine. This invention relates to
improvements in the production of coloring matters, and more
especially to improvements in the method of producing what is known
as artificial alizarine, from anthracine, a method of producing
which was described in"
the English patent of December 18, 1868, and in No. 95,465,
"and consisted in the production of artificial alizarine by
converting anthracine into either bibromanthrakinon or
bichloranthrakinon, and then acting upon the same by means of an
alkali and precipitating the alizarine contained in the alkaline
solution by means of an acid. In the complete specification of the
aforesaid letters patent granted to Charles Liebermann and Charles
Graebe, two different series of processes are described for
obtaining the brominated or chlorinated derivatives of anthrakinon.
In the first of these processes, the anthracine is submitted to the
action of oxidizing agents, as is well understood, and the oxidized
anthracine or anthrakinon is then treated with bromine or chlorine.
In the second of these processes, the anthracine is first treated
with bromine or chlorine, and subsequently submitted to an
oxidizing process in order that the desired compounds,
videlicet bibromanthrakinon or bichloranthrakinon, may be
obtained. In an analogous manner, we now employ sulphuric acid as a
substitute for the bromine or chlorine employed in the processes
above referred to, and we thus obtain the sulphuric acid
derivatives of anthrakinon, which we call the sulpho-acids of
anthrakinon."
The specifications then go on to describe the two new processes.
The first is to alter the anthrakinon by heating it with sulphuric
acid. The product is then put in solution and treated with
carbonate of lime, and then with carbonate of potash or of soda,
and potash or soda salts of the sulpho-acids of anthrakinon are
produced. These are treated with caustic soda or potash under heat,
and the artificial alizarine is precipitated by an acid. In the
second process, anthracine is heated with sulphuric acid, the
product is put in solution and treated with peroxide of manganese
under heat. Caustic lime is then added in excess till there is an
alkaline reaction, the mixture is then filtered, and carbonate of
potash or soda is added to it and the potash or soda salts of the
sulpho-acids of anthrakinon are produced.
Page 111 U. S. 308
These are treated with caustic potash or soda under heat, the
product is put in solution, and the artificial alizarine is
precipitated by an acid. It is stated in regard to this substance,
made by either of these two processes, that it "may be employed for
the purposes of dyeing and printing, either in the same way as
preparations of madder are now used or otherwise." In each of the
two specifications there are two claims in these words:
"1. The manufacture of coloring matters by submitting
anthrakinon to the action of sulphuric acid so as to obtain soluble
compounds, which we have called sulpho-acids of anthrakinon,
treating the products of such operation with an alkali, and
precipitating the coloring matters therefrom by means of an acid,
as herein described. 2. The manufacture of coloring matters by
submitting anthracine to the action of sulphuric acid, oxidizing
the product thereby obtained, heating such oxidized product with an
alkali, and subsequently precipitating the coloring matters
therefrom by means of an acid, as herein described."
After the granting of the English patent for the sulpho-acid
process, on June 25, 1869, to Graebe and Liebermann, and their
application for the United States patent on January 26, 1870, it
became apparent that the sulpho-acid processes and products were to
be commercially valuable. Then, during the interval of the four
years and a half delay in the issuing of No. 154,536, No. 95,465
was surrendered and reissued in two parts April 4, 1871, one for
the process and the other for the product, the claim in the latter,
No. 4,321, being so worded as to cover
"artificial alizarine, produced from anthracine or its
derivatives, by either of the methods herein described, or by any
other method which will produce a like result."
Afterwards Graebe and Liebermann assigned the two reissued
patents of April 4, 1871, to the plaintiff, on March 1, 1872.
It is very plain that the specification of the original patent,
No. 95,465, states the invention to be a process for preparing
alizarine, not as a new substance prepared for the first time, but
as the substance already known as alizarine, to be prepared,
however, by the new process, which process is to be the subject
of
Page 111 U. S. 309
the patent, and is the process of preparing the known product
alizarine from anthracine. The specification states that "the
alizarine" is precipitated, that "the yellow flocks of alizarine"
are obtained, and that "the alizarine" is in such a form that it
can be employed in the same manner as the different preparations
from madder, and the claim is for the "process for the production
of alizarine." The provisional specification deposited in England,
December 18, 1868, states that "yellow flocks of alizarine are
precipitated," and that "the alizarine prepared in this artificial
way is perfectly pure;" and the full specification, filed in
England, June 17, 1869, claims "the artificial production of
alizarine." No other conclusion can be reached than that Graebe and
Liebermann, in the specification of No. 95,465, intended by
"alizarine" the chemical substance known by the formula C14H8O4,
and thought that was what their process produced. There is no
suggestion of anthrapurpurine or isopurpurine, or of any process
for producing them. Their published statements show that it was the
synthesis of the alizarine of madder which they were making -- the
specification of No. 95,465 shows that and nothing else -- and it
is not contended that the alizarine of madder contains
anthrapurpurine or isopurpurine. It is very clear from the
testimony, that it is to anthrapurpurine or isopurpurine that the
artificial alizarine sold by the defendants owes its efficiency as
a dyestuff and its practical success in the market, and that such
product is produced by the bisulpho-acid process of Perkin, and it
is not satisfactorily shown that the monosulpho-acid process of
Caro or the bromine process of No. 4,321 will either of them
practically produce that product.
Inasmuch as the defendant's article is produced from anthracine
or its derivatives by some method, and is a dyestuff called
artificial alizarine, it is contended that the sale of it infringes
No. 4,321. The articles in market, called artificial alizarine at
the present day, are substances all of which are made from
anthracine, but they vary all the way from nearly pure alizarine,
made by the monosulpho-acid process, through the products of the
bisulpho-acid process, which contain combinations of alizarine and
anthrapurpurine, up to an article of pure
Page 111 U. S. 310
purpurine, free from alizarine. All of these are used as
dyestuffs, according to the shade of color and other qualities
desired. The specific article put in evidence in this case as an
infringement contains about sixty percent of anthrapurpurine. It is
claimed by the plaintiff to be the artificial alizarine described
in No. 4,321, and to be physically, chemically, and in coloring
properties similar to that. But what that is is not defined in No.
4,321, except that it is the product of the process described in
No. 4,321. Therefore, unless it is shown that the process of No.
4,321 was followed to produce the defendant's article, or unless it
is shown that that article could not be produced by any other
process, the defendant's article cannot be identified as the
product of the process of No. 4,321. Nothing of the kind is shown.
On the other hand, the defendant's article is made abroad, and by a
process different from that of No. 4,321. It therefore cannot be
the product of that process. If the words of the claim "by any
other method which will produce a like result" mean any other
method which will produce the only product mentioned in the
description, namely, alizarine, as then understood, having the
formula C14H8O4, the defendant's article is not that product, for
it contains other dyeing ingredients which the alizarine of the
patent does not contain. If the words of the claim are to be
construed to cover all artificial alizarine, whatever its
ingredients, produced from anthracine or its derivatives by methods
invented since Graebe and Liebermann invented the bromine process,
we then have a patent for a product or composition of matter which
gives no information as to how it is to be identified. Every patent
for a product or composition of matter must identify it so that it
can be recognized aside from the description of the process for
making it, or else nothing can be held to infringe the patent which
is not made by that process.
The circuit court found as a fact that the defendant's article
was produced by the process described in No. 154,536. But it
regarded that process as the same process chemically as the process
of No. 4,321, on the view that the bromine used in the latter was
merely a vehicle, and in the former sulphuric acid
Page 111 U. S. 311
was substituted as a vehicle, and, though superior, performed
the same office in the same way, and so, as it regarded the two
processes as the same, it held the two products to be the same. We
consider it, however, to be established that the defendant's
article is not made by the process of No. 4,321, but is made by the
bisulpho-acid process of Perkin, which yields anthrapurpurine, and
which, while it may involve the process of No. 154,536, goes beyond
it. The bisulpho-acid process puts in two atoms of anhydrous
sulphuric acid instead of one, and additional oxygen is carried in,
and anthrapurpurine is produced, the formula of which is C14H8O5.
Aside from this, it is shown that the dyeing qualities of the
defendant's article depend on the anthrapurpurine or isopurpurine
it contains, and not on the alizarine. As the only alizarine
mentioned in No. 95,465, or in No. 4,321, is alizarine the formula
of which is C14H8O4, the alizarine of madder, the process described
in those patents, to be a sufficient support for a valid patent, as
being properly described, must be a process which will produce that
article and no other, and No. 4,321, to be valid as a patent for a
product, must be a patent which will produce, by the process it
describes, that article and no other. Unless that process will
practically produce the defendant's article, No. 4,321 is not
infringed, and it is not established, by the evidence, that it
will.
There is another view of the case. According to the description
in No. 95,465, and in No. 4,321, and the evidence, the article
produced by the process described was the alizarine of madder,
having the chemical formula C14H8O4. It was an old article. While a
new process for producing it was patentable, the product itself
could not be patented, even though it was a product made
artificially for the first time, in contradistinction to being
eliminated from the madder root. Calling it artificial alizarine
did not make it a new composition of matter, and patentable as
such, by reason of its having been prepared artificially, for the
first time, from anthracine, if it was set forth as alizarine, a
well known substance.
Wood Paper
Patent, 23 Wall. 566,
90 U. S. 593.
There was therefore no foundation for reissue No. 4,321, for the
product, because, on
Page 111 U. S. 312
the description given, no patent for the product could have been
taken out originally.
Still further, the claim of No. 4,321 is not a claim merely for
the product of the process described in it, but is a claim for
anything which may be called artificial alizarine, produced from
anthracine, or its derivatives, by either of the methods described,
or by any other method, equivalent or not, which will produce
anything called artificial alizarine. The scope of such a claim is
seen in this suit. An article is sought to be covered, by the
reissue, which, it is demonstrated, Graebe and Liebermann never
made by their bromine process, which they knew that process would
not produce, which they recognized as produced first by some one
else, by a different process, and which has become the subject of a
large industry abroad, and an extensive use in this country,
through discoveries made, as they acknowledge, since their bromine
process was invented. After those discoveries were made, after it
was seen that the bisulpho-acid process would produce desirable
dyestuffs, and could be worked practically and profitably to that
end, it was sought to control the market for the product in the
United States by obtaining this reissue No. 4,321.
We have not deemed it necessary to consider more particularly
the question whether the reissued patent, No. 4,321, is or is not
for a different invention from that described in the original
patent. It certainly is, unless the product claimed in the reissue
is precisely that product, and no other, which the process
described in the original patent produces. There can be no better
evidence, as against the appellee, of what that product is, than
the declarations of the original patent itself, and of the
patentees elsewhere, as already shown. Nor have we deemed it
necessary to inquire or determine whether, even if the product
claimed in the reissue were the same as that which the process
described in the original patent produces, it could have been made
the subject of a reissued patent at the time when, and under the
circumstances in which, this reissue was made. It is so clear that
the defendants are not shown to have infringed that we have not
deemed it necessary to consider other questions any further.
Page 111 U. S. 313
It results, from these considerations, that if the claim of No.
4,321 is to be construed so broadly as to cover the defendant's
article, it is wider in its scope than the original actual
invention of Graebe and Liebermann, and wider than anything
indicated in the specification of the original patent, and that, if
it is to be construed so as to cover only the product which the
process described in it will produce, it is not shown that the
defendant's article is that product, or can be practically produced
by that process. In either view.
The decree of the circuit court must be reversed, and the
case be remanded to that court, with direction to dismiss the bill
of complaint.